Top 10 articles are a dime a dozen and often quite subjective. We wanted to create a top 10 list of the best small city road trip destinations that would be fair and worthy of being on such a list. So, we enlisted the world’s most road tripped man, Mike of MikesRoadTrip.com, to give us some of his favorite road trip destinations. From there, the public had a month to vote on their favorite small city road trip destination. With over 2,500 votes, these are the places YOU voted as the 10 best small city road trip destinations in the U.S.

Top-10 Best small city road trip destinations for 2018. Photo by Mike Shubic of MikesRoadTrip.com

Let the open road be your guide! | Photo: Mike Shubic of MikesRoadTrip.com

I have road tripped all over the U.S. As a matter of fact I’ve been to 49 of the 50 states, only the last frontier of Alaska eludes me. Needless to say, I’ve had an opportunity to visit many amazing small cities around the country. This list will absolutely inspire a road trip; each destination featured has its own unique attributes. So rent a car and join me on an amazing road trip adventure!

In order to make the list, each of the cities had to possess much of the following criteria:

  • Combination of high-end and unique lodging options
  • Fantastic restaurants
  • Cultural significance
  • Good selection of amenities
  • Awe-inspiring sights or scenery
  • Some level of uniqueness and/or be remarkable
  • Outdoor and indoor activities

Without further ado, I present the Top 10 Small City Road Trip Destinations in the U.S. for 2018:

#10 Fairhope/Point Clear, Alabama (Tied for #10 with 98 votes)

The Fairhope/Point Clear area is located along Mobile Bay near the Gulf Coast. It is a place that bestows grandeur and southern charm with some scenery that is almost idyllic. The streets are lined with massive oak, cypress and maple trees, each woven with a confetti of ivy and Spanish moss. The sun has a difficult time piercing the denseness that blankets the trees, but when it does, sun-flares sparkled in a way that makes you feel like you’re driving through the scene straight out of a storybook.

The coast is dotted with docks and boathouses, one right after the other. The homes are finely crafted in a style that could best be described as southern cottage. The look of the area is unique (at least it was to me), so much so that I had to wonder if it was indigenous to the Gulf Coast. You’ll be enamored by the unique beauty that surrounds the Fairhope and Point Clear area.

Closest Major City: Mobile, Alabama (20 miles)
Closest Major Airport: Pensacola, Florida (55 miles)
Lodging Recommendations: Grand Hotel – This historic Alabama Gulf Coast hotel was built in 1847 and has a fascinating story with an outstanding location.
Recommended Restaurants: Panini Pete’s, Market by the Bay, R Bistro and Saltwater Grill. Many other great looking restaurants, I just didn’t get a chance to try them all.
Don’t Miss: Driving the coast — stop by Mullet Point Park, Pelican Point, South Beach and Knoll Parks. If you have a sweet tooth, be sure to stop by Punta Clara Kitchen, a decadent candy shop.

Fairhope Alabama one of the best small city road trip destinations for 2018. Photo by MikesRoadTrip.com

Fairhope/Point Clear, Alabama | Photo: Mike Shubic of MikesRoadTrip.com

#10 Jackson, New Hampshire (Tied for #10 with 98 votes)

Jackson is one of the smaller cities on this list with a population of less than 1,000, however what it lacks in size, it makes up for in grandeur. The bright red covered bridge that one must pass through to enter Jackson sets the stage for something special. Nestled within the White Mountains of New Hampshire, Jackson offers a lot of stunning scenery to explore. From the seemingly endless cascade of Jackson Falls, to the highest point in all of New England up the Mt. Washington Auto Road, to the myriad hikes, snow skiing, kayaking, river rafting to the countless waterfalls, this region of New Hampshire is a mecca for outdoor enthusiasts.

Jackson is a place to get away from it all and yet feel right at home. The charming community has been attracting guests for over 200 years. There are many great lodging choices and some fantastic restaurants nearby.

Closest Major City: Portland, Maine (73 miles)
Closest Major Airport: Boston Logan (147 miles)
Lodging Recommendations: In nearby Conway is one of the coolest and most unique hotels I’ve ever seen. It’s called Adventure Suites and each room has a completely different over-the-top theme — from the Cave to the Haunted Castle to the Club, complete with a disco dance floor and top-notch sound system. Right in Jackson is the Snowflake Inn, a regal structure situated on six acres that offers guests an at-home experience.
Recommended Restaurants: Cider Co and 1785 Inn & Restaurant.
Don’t Miss: The drive up Mt. Washington.

Jackson New Hampshire is one of the best small city destinations for 2018. Photo by: Mikes Shubic of MikesRoadTrip small city road trip destination

Jackson, New Hampshire | Photo: Mike Shubic of MikesRoadTrip.com

#9 Leavenworth, Washington (5% of the vote)

Leavenworth is a Bavarian-themed community, and when I say “themed,” I mean embraced through-and-through — from its architecture to the attire. The look/feel of Leavenworth is reminiscent of a hillside community along the banks of the Rhine River. With over 700 miles of hiking, biking, and horseback riding trails, you can devour nature. Or, you can relax at one of the many luxurious lodging choices in town, several right next to the Wenatchee River (the West’s version of the Rhine!). If you’re into spas, theater, festivals, geocaching, wine tours, museums, or drinking beer from a stein, you’ll find that too.

Leavenworth is also well known for its holiday festivities, with millions of lights, sleigh rides, sledding right in town and carolers walking the streets spreading cheer. In the winter, snow skiing is just up the hill at Stevens Pass. Leavenworth is a four-season destination with some top-notch lodging, spas, restaurants and an abundance of outdoor activities.

Closest Major City: Seattle, Washington (134 miles)
Closest Major Airport: SeaTac International Airport (140 miles)
Lodging Recommendations: Run of the River Inn & Refuge is a secluded and romantic location just outside of town. Bavarian Lodge is right in town and within walking distance to everything.
Restaurant Recommendations: Viscontis, Watershed, Manna, SOUTH, Pavz Cafe/Bistro, and Munchen Haus for some authentic German food.
Don’t Miss: The Holiday Season.

Leavenworth Washington one of the best small city road trip destinations for 2018

Leavenworth, Washington | Photo: Mike Shubic of MikesRoadTrip.com

#8 Eureka Springs, Arkansas (5% of the vote)

Eureka Springs is a Victorian mountain village nestled in the Ozarks with copious things to see and do. You can zip-line through the forest, watch big cats feed at a wildlife refuge, view breathtaking vistas and scenic overlooks, fish in clear trout streams, photograph waterfalls or stroll through the colorful gardens surrounding an ancient burial ground — if that doesn’t make your spirits soar, check out one of the famous haunted houses. To stir the soul further, head into downtown for some live music at any number of venues — one of the best spots is Basin Park for frequently free community concerts.

If you’re into shopping, there are over 100 boutique shops and galleries. If you like staying at inns and B&B’s, Eureka Springs is said to have more per capita than any place in the country. Eureka Springs always seems to have something going on, from festivals to concerts; it’s a place that has a contagious energy.

Closest Major City: Springfield, Missouri (83 miles)
Closest Major Airport: Kansas City Airport (248 miles)
Lodging Recommendations: Cliff Cottage Inn is a cluster of bungalows located on a hillside overlooking downtown. There are eight rooms from which to choose from—each themed and named for a well-known author. Grand Central Hotel is a historic property located right in the heart of town with a great on-site restaurant.
Restaurant Recommendations: Local Flavor Cafe, Grand Taverne, Mud Street Cafe and Thai House Restaurant.
Don’t Miss: Blue Spring Heritage Center.

Eureka Springs Arkansas is one of the best small city road trip destinations for 2018

Eureka Springs, Arkansas | Photo: Mike Shubic of MikesRoadTrip.com

#7 Charlottesville, Virginia (6% of the vote)

Charlottesville is located along the foothills of the Blue Ridge Mountains. During its long and illustrious existence, Charlottesville (aka C’Ville) has been able to maintain its small town charm. C’Ville has churned out three U.S. Presidents, including our third, Thomas Jefferson, whose presence is still felt, remembered and revered. As a matter of fact, the University of Virginia was founded by Thomas Jefferson and is located right in the heart of C’Ville.

The focal point of the community is the Downtown Mall, where on Saturdays you’ll find many of the local restaurateurs buying their ingredients at the farmers market. You’ll also discover a rich art scene, over 20 wineries and some award-winning small-batch breweries to explore. With its fertile land and over 200 restaurants, Charlottesville is at the center of the culinary food scene, with many of the chefs and restaurants receiving national recognition. There are also some fantastic lodging choices, historical sites and a plethora of activities in Charlottesville, making it without question one of the best small city road trip destinations in the country.

Closest Major City: Richmond, Virginia (71 miles)
Closest Major Airport: Dulles Airport (102 miles)
Lodging Recommendations: Boar’s Head Resort or Clifton Inn.
Restaurant Recommendations: The Local, Clifton Inn, MAS Tapas, Brookville Restaurant, CO, and The Whiskey Jar.
Don’t Miss: Monticello – Thomas Jefferson’s amazing estate.

Charlottesville, Virginia is one of the best small city road trip destinations for 2018. Photo by Mike Shubic of MikesRoadTrip.com

Charlottesville, Virginia | Photo: Mike Shubic of MikesRoadTrip.com

#6 Durango, Colorado (7% of the vote)

Durango is a city that has it all, from city life, outdoor experiences to culinary delights. With water activities, bike and walking trails, to a nearby ski resort, there is no wrong time of year to visit. If you’re into adventure, Durango has you covered with zip-lining, hiking, biking, rafting, skiing, dude-ranches and a whole lot more. Looking for a more low-key experience? Walk the well-preserved historic streets lined with unique shopping and restaurants. Need a break from the walk? Pop into one of many local breweries for a taste of Durango. Or, hop on the Durango & Silverton train for a number of seasonal rides to see the area’s stunning landscape.

Durango is ideally positioned for outings to Mesa Verde National Park, Vallecito Lake and other natural surroundings, which will keep you captivated during your visit. Green trees in the spring, stunning autumn leaves in the fall and snow-covered branches in the winter make Durango one of the best small city road trip destinations in the country.

Closest Major City: Albuquerque, New Mexico (215 miles)
Closest Major Airport: Albuquerque International Sunport (218 miles)
Lodging Recommendations: The General Palmer Hotel and Strater Hotel are nice historic properties right in downtown. The Blue Lake Ranch is also an excellent choice a bit outside of Durango on a secluded 200-acre ranch.
Restaurant Recommendations: Ken & Sue’s, Mahogany Grill, Ore House, and Carver Brewing Co for breakfast.
Don’t Miss: Riding the rails of the Durango & Silverton Narrow Gauge Train.

Durango, Colorado is one of the best small city road trip destinations for 2018. Photo by Mike Shubic of MikesRoadTrip.com

Durango, Colorado | Photo: Mike Shubic of MikesRoadTrip.com

#5 Bozeman, Montana (7% of the vote)

Bozeman is nestled within the Gallatin Valley of the western Rocky Mountains, perfectly positioned for excursions to Yellowstone National Park, Chico Hot Springs, Hyalite Canyon or the Lewis & Clark Caverns. Surrounded by pristine rivers and nature’s magnificent canvas of trees, majestic mountains, rippling waterfalls, and open prairies of wildlife moseying through their day make Bozeman an incredible small city road trip destination.

Slip out of your hiking or fishing gear and into evening attire for a show at the 1900’s Ellen’s Theater. Once known as a major stop for the Vaudeville circuit, its gilded carvings add an ambiance of elegance as you watch the performance. Bozeman has some superb lodges and guest ranches that really embrace the wide-open space and cowboy western flair.

Closest Major City: Billings, Montana (141 miles)
Closest Major Airport: Spokane International Airport (405 miles). Bozeman has a pretty large airport as well.
Lodging Recommendations: If you’re looking for a 5-star lodge experience, check out The Gray Cliffs Ranch (Note: 30 miles west of Bozeman). The LARK hotel in downtown Bozeman is centrally located and embodies a Montana feel with a modern take. About 15 minutes west of Bozeman is the Gallatin River Lodge, which offers fly-fishing, a fantastic restaurant, and other activities.
Recommended Restaurants: Cafe Fresco delights with a rich Italian menu and cozy atmosphere. Gallatin River Lodge for outstanding food harvested in the nearby area.
Don’t Miss: Fly Fishing! Or, a hike to an 80-foot thunderous waterfall known as Palisade Falls.

Bozeman Montana is one of the best small city road trip destinations for 2018. Photo by: Mike Shubic of MikesRoadTrip.com

Bozeman, Montana | Photo: Mike Shubic of MikesRoadTrip.com

#4 Port Orford, Oregon (10% of the vote)

Port Orford is so small, that if you blink, you might just pass right through town and not even realize it.  Regardless of its small stature, this southern Oregon coastal community has much to offer. Port Orford is one of those proverbial, “diamond in the rough” destinations. One does not typically expect such wonderful amenities from a smaller town, but this coastal community is not only worth a stop, it’s worth a stay. With a vibrant art scene hosting over a dozen galleries, a number of quality restaurants and some outstanding accommodations, Port Orford would make any discerning traveler feel comfortable.

The art galleries trend from the whimsical, to the ultra-modern. There are several lovely B&Bs in town, some offering individual romantic cabins in a tranquil setting coupled with rugged and ocean views. You will also find several tasty places to eat … from the high-end, to the eccentric. You won’t get bored either. Heads State Park is a great place for hiking and unobstructed ocean views, while Agate Beach offers a wonderfully long stretch of sandy beach … great for flying a kite, romantic strolls or lying out on a warm summer day.

Closest Major City: Medford, Oregon (193 miles)
Closest Major Airport: Portland International Airport (274 miles)
Lodging Recommendations: Redfish Loft.
Restaurant Recommendations: RedFish and Crazy Norwegians.
Don’t Miss: Heads State Park and Humbug Mt. State Park just south of Port Orford.

Port Orford Oregon is one of the best small city road trip destinations for 2018. Photo by Mike Shubic of MikesRoadTrip.com

Port Orford, Oregon | Photo: Mike Shubic of MikesRoadTrip.com

#3 South Lake Tahoe, California (12% of the vote)

South Lake Tahoe is a magnificent mountain town situated along the banks of a breathtaking body of water that has inspired artists and attracted aquatic and snow enthusiasts for generations. South Lake Tahoe straddles California and Nevada within the rugged Sierra Nevada range, which makes a road trip to this small city destination one filled with delight and amazement.

The area can accommodate anyone’s taste or style, from cool cottages, modern motels, boutique inns to sophisticated beachside resorts. No matter the season, outdoor enthusiasts will rejoice with the abundance of activities at their fingertips. Located within the village center is the Heavenly Gondola, taking skiers and sightseers up a mountain face that provides striking views for as far as the eye can see. Outdoor patios with live music emanating from the many bars and restaurants provide a lively atmosphere that draws visitors into its recreational cocoon.

Fantastic dining, entertainment, activities, an array of lodging choices and scenic drives make South Lake Tahoe one of the best small city road trip destinations in the country. 

Closest Major City: Reno, Nevada (62 miles)
Closest Major Airport: Reno International Airport (58 miles)
Lodging Recommendations: Edgewood Resort offers uncompromising luxury accommodations. The Coachman is a hip modern motel/hotel near the Village.
Restaurant Recommendations: Sage Room Steak House, Freshies, Azul Latin Kitchen, Cold Water Brewery & Grill, Driftwood Café (great breakfast place), Lake Tahoe Aleworx.
Don’t Miss: Driving to Emerald Bay. Historic sights, hikes and stupendous views await along this scenic drive.

South Lake Tahoe is one of the best small city road trip destinations for 2018. Photo by Mike Shubic of MikesRoadTrip.com

South Lake Tahoe, California | Photo: Mike Shubic of MikesRoadTrip.com

#2 Chattanooga, Tennessee (16% of the vote)

Chattanooga, like many historic towns across the country, has gone through a re-birth over the past couple of decades. The preface of Chattanooga’s revitalization can be attributed to the development of a world-class aquarium that spawned a downtown renaissance. What has followed is a thriving art scene, including gastronomy, lots of live music and annual events. There is also a cornucopia of outdoor activities, such as the flight park for hang gliding, rock climbing/bouldering, kayaking and mountain biking.

Just outside of town is Lookout Mountain where there are a number of major attractions, from Ruby Falls (a waterfall deep inside a mountain cave), Incline Railway (a thrilling 1-mile train ride up the mountain) to one of my favorite attractions in all of Chattanooga, Rock City. Resting at the foothills of the Appalachian Mountains and alongside the Tennessee River, Chattanooga is absolutely one of the best small city road trip destinations in the country.

Closest Major City: Atlanta, Georgia (118 miles)
Closest Major Airport: Hartsfield-Jackson Atlanta International Airport (127 miles)
Lodging Recommendations: The Dwell Hotel, The Read House Historical Inn & Suites.
Restaurant Recommendations: Broad Street Grill for sophisticated dining, Public House for hip and upscale, and The Flying Squirrel for eclectic Southern comfort food.
Don’t Miss: Rock City, an amazingly unique botanical garden. The Tennessee Aquarium, one of the best in the country.

Chattanooga Tennessee is one of the best small city road trip destinations for 2018. Photo by Mike Shubic of MikesRoadTrip.com

Chattanooga, Tennessee | Photo: Mike Shubic of MikesRoadTrip.com

#1 Walla Walla, Washington (18% of the vote)

And, the number one small city road trip destination for 2018 is Walla Walla, Washington. It’s so nice; they had to name it twice!

Walla Walla may have been known as a college town and farming community famous for its sweet onions, however it has fast become known for its quality soil to grow world-class grapes. Twenty years ago, Walla Walla had 20 wineries. Today, there are over 140! This explosion into the wine industry has attracted top-notch chefs who’ve opened many stellar restaurants. The growth has also spawned some outstanding lodging choices, from the completely renovated historic Marcus Whitman, to a slew of high quality inns and B&Bs.

When you approach Walla Walla for the first time, you will likely wonder if you’re in the right place as the land looks barren and unassuming. However, as you get closer, you’ll see the charm of rolling wheat fields, tree-lined streets with craftsman style homes and manicured vineyards. The downtown area is full of historic buildings and endearing people. As a matter of fact, back in 2011, Walla Walla was crowned “most friendly” small town in America by Rand McNally and USA Today.

Closest Major City: Spokane, Washington (153 miles)
Closest Major Airport: Spokane International Airport (153 miles)
Lodging Recommendations: Marcus Whitman is a stunning hotel right in town with a fantastic restaurant. Cameo Heights Mansion in a romantic boutique inn just outside of Walla Walla. They too have a great on-site restaurant.
Restaurant Recommendations: The Marc (inside the Marcus Whitman), T Maccarone’s, Brasserie Four, Graze and the Maple Counter Cafe is a fantastic place for breakfast.
Don’t Miss: Wine Tasting! Walla Walla is for wine lovers. Hot air balloon ride.

Walla Walla Washington is one of the best small city road trip destinations for 2018. Photo by: Mike Shubic of MikesRoadTrip.com

Walla Walla, Washington | Photo: Mike Shubic of MikesRoadTrip.com

Each of these small city road trip destinations has something unique and wondrous to offer. If you’ve ever road tripped to one of these small cities, leave a comment below and share your experience and/or suggestions.

Mike Shubic of MikesRoadTrip.com is an official Travelocity Gnational Gnomad. Gnational Gnomads is an exclusive group of high-profile travel and lifestyle experts who offer tips and inspiration on behalf of Travelocity.

Travelocity compensates authors for their writings appearing on this site; such compensation may include travel and other costs.

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